Dyeing of materials made of or containing cellulose derivatives



Patented Nov 19, 'ieae'.

This invention relates to the dyeing, printcellulose derivatives are hereinafter referred.

to as organic substitution derivatives of cellulose.

' This application is a division of my prior ap lication No. 175,012, filed March 12, 1927.

' ccording to this invention materials made with or containing one or more of the said organic substitution derivatives of cellulose are dyed or otherwise colored with'coloring matters or compounds containin one or more thiourethane or substituted t ionrethane residues, that is coloring matters or compounds in which an aryl dye nucleus or component thereof is linked directly or indirectly to the nitrogen atom of any ester of sulpho-carbamic acid, or of substituted sulpho-carbamic acids. v

Further according to the present invention such coloring matters may be formed on the fibre or material by combination. of components, one or more of which contain such thiourethane or substituted thiourethane residues.

The compounds for use according to the present invention may be prepared by any convenient method. Thus for example they may be prepared by heating the correspon d- 7 ing isothiocyanate compounds with alcohols or alkali metal alcoholates or mixtures thereof or. with alcoholic caustic alkali, by treating' the corresponding thiourea chloride com,-

pounds with alcohols or alkali metal alcoholates or mixtures'thereof, orby treatingv a halogen compound containing an aryl dye nucleus-or component thereof with an ester of sulpho-carbamic acid. Further in some or on cause cnnnunosn nirnnn vrit' n's I No Drawing. origlnalfapplicaticn filed Hatch 32,1927, Serial Ho. 175,019,

14, 192% Divided and this application filed. January 30,

ms. Serial 11. 250,150.

cases the thiourethane prepared by prolonged. com ound w1th an alcohol, and carbon b'isul de il he following examples of coloring mat-e ters or compounds for use according to the present-invention and of the methods of preto be illustrative paring them are intended and not in any way limitative.

A. Anthmquinone dyestufis' compounds may be boiling of an amino and in Great Britain December Example '1.1 acetylamino anthr'aquinone-4-isothiocyan'ate is heated with ethyl val-- alcoholic potash to obtain't-he' s i v cohol or with dyestufi Example 2-13enzeneeazo-u-naphthylamine is diazotized and coupled-with the. net obtained by boiling salicylic acid-5-thiocyanate with alcoholic potashto obtain a dyestuif of the formula i coon Azo dyestufismay be produced on the fibre or material in a similar manner by the couprodpling of components (base or aminoazo compound and developer) one or more of which contains thiouret ane'residues.

The "dyestufi's or compounds maybe applied in aqueous solution (whereth ey are sufiiciently soluble) and I prefer to emplo this method when possiblj. The dyestu s or compounds may be made more soluble by the introduction 'of side chains containing one, two, three or more 'hydroxy groups for example side chains of the type described in U. S. a plications S. No. 162,936 and S. N 0.16293? When, however, the dyestuffs or compounds by by iiissolvingin a' soluble they=. may he apare not sufliciently plied to the goods-maqueoussuspension or in colloidal solutions or dispersions" obtain nding (for example-1n colloid mills),

water containing or not containing protectlve colloids, by pretreat' the coloring .mat

tersor compounds wit '"solubilizing agents or by other methods. 0f; the solubilizm" agents which are suitable =fo-r' obtaining sue dis "ersionsI maiy" mention those-describ 1%. s. Patents os.-1,618,4=13 and 1,618 414 and U. S. application S. No. 50,525, an in British PatentsNos. 273,819 and 27 3,820 and the corresponding U. S. aptplications S. Nos. 134,138 and 176,289; viz odies of oil? fatty characteristics namely higher a acids or sulphonated or other derivatives thereof containing salt forming grou s, such as sulphoricinoleic acid or other sulp onated fatty acids or salts of such acids or bodies, for instance their alkali or ammonium salts,

used alone'or in con'unction with auxiliary .solvents as describe in U. S. applications S. No. 48,666 and S. No. 152,517 carbocylic compounds containing in their structure one or more salt forming groups or salts of such compounds; sulpho-aromatic fatty acids or I salts thereof; and soluble resin soaps or sotan or compounds 1n WhlCh directly or indirectly ters or comsolmds of these groups,

dium or other soluble salts or other soluble salts of resin acids.

Though coloring matters and compounds belongin to particular groups have been describe above, it is to be understood thatlimited to coloring matbut comprises broa ly the application to materials made of\or containing cellulose acetate or other of the tution derivatives of cellulose of the invention is not coloring matan a nucleus or component thereof is linke either to one or more thiourethane or substitut In the case of using components of aryl (1%: nuclei the actual coloring matters may produced on the fibre or material.

' Mixed goods containing for examsle, in addition to the or ariic substitution erivative or derivatives 0 cellulose,

fibres or threads, may be dyed or otherwise colored with or without employment of other d estufis or components according to the c aracter of the being applied if desired before 'or a er the application of the coloring matters or compounds of the present invention, or when not deleteriously afiected thereby, they may be applied in conjunction therewith.

The term dyein in the claims is'to be understood to inclu e printing and stenciling and also to include the case when the actual dye compound is produced on the material solvent and pouring'into thiouret ane residue.

or tty I ing herein described organic substi- Y dye thiourethane residues.

cotton, silk, wool,.. 'or the cellulose type of artificial silk or other threads or fibres used in association, said other dyestufis or com onents memes.

itself-by-interaetion of components, as for I example when dyein b the azoic rocess. What I claim and desire to secure y Let-- ters Patent is:- (1 1.- Process for dyeing 'materialcomprising an organic substitution derivative of co lulose, comprising dyeinfilthe material with a color-' ing com ound w 'ch comprises at least one 2.- Process according to claim 1, characplied in aqueous solution.

3; Process according to claim 1, characterized in that the coloring compound is applied in aqueous colloidal solution.

4. Process according to claim 1, characterized in that the coloring compound is applied in aqueous cplloidal 50111131011 obtained y pretreatmg the compound with a solubilizagent.

5. Process for dyeing material com rising an organic substitution derivative 0 cell lose, comprising d ein the material with a coloring compoun I one substituted thiourethane residue.

'6. Process for dyeing material com rising an organic substitution derivative 0 cellulose, comprisingdyeing thematerial with an azo coloring com ound which comprises at least one thiouret ane residue.

7. Processfor dyeing material com rising cellulose acetate, comprising dyeing t e materialwith a coloring compound which comprises at least one thiourethane residue.

8. Process according to claim 7, characterized in that the coloring compound is applied in aqueous solution.

9. Process according to claim 7, characterized in that the coloring compound is applied in aqueous colloidal solution.

10. Process according to claim 7, characterized in that the coloring compound is ap- Elied in aqueous colloidal solution obtained y pretreatmg the compound with a solubilizterized in' that the coloring compound is apwhlch comprises at least dyed with a q In testimony whereof I have hereunto subv scribed my name.

HE'NRY'DRE'YFUS'. 

